Bis(trimethylsilyl)methylamine (BSMA): tool or toy?

2000 ◽  
Vol 78 (11) ◽  
pp. 1363-1379 ◽  
Author(s):  
Jean-Paul Picard
Keyword(s):  
Primary Amine ◽  
Nitrogen Heterocycles ◽  
Biological Properties ◽  
Methine Proton ◽  
Mild Conditions ◽  
Synthetic Intermediates ◽  
Synthetic Methodologies

Bis(trimethylsilyl)methylamine, BSMA, an original primary amine, was proven to be the source of a large variety of N-bis(trimethylsilyl)methylamino derivatives that otherwise have to be prepared indirectly. Because of the bulkiness of the bissilylmethyl group, regio- and stereoselectivities resulted in appropriated examples. Apart from the potential biological properties associated with the Si-C-N framework, these derivatives were powerful synthetic intermediates. Special emphasis was given to the chemistry of corresponding imines. Cleavage of Si—C bonds or abstraction of the methine proton afforded α-nitrogen carbanions in very mild conditions. Application of these results to the β-lactam chemistry allowed the introduction of new synthetic methodologies in this field. It results the (Me3Si)2CH- group could now be regarded as a Me3SiCH2- or a CH3- group or a proton equivalent.Key words: bis(silyl)methylamine, preparations, reactivity, nitrogen heterocycles, α-nitrogen carbanions.

A Review on Biological Properties and Synthetic Methodologies of the Diarylpentadienones

2020 ◽  
Vol 20 ◽  
Author(s):  
Maryam Aisyah Abdullah ◽  
Siti Munirah Mohd Faudzi ◽  
Nadiah Mad Nasir
Keyword(s):  
Biological Properties ◽  
Review Article ◽  
High Potential ◽  
One Pot ◽  
One Pot Synthesis ◽  
Structure Activity ◽  
Synthetic Methodologies ◽  
Relationship Of ◽  
Effective Drugs ◽  
Enhanced Stability

Abstract:: Medicinal chemists have continuously shown interest in new curcuminoid derivatives, the diarylpentadienones, owing to their enhanced stability feature and easy preparation using a one-pot synthesis. Thus far, methods such as Claisen-Schmidt condensation and Julia-Kocienski olefination have been utilised for the synthesis of these compounds. Diarylpentadienones possess a high potential as a chemical source for designing and developing new and effective drugs for the treatment of diseases, including inflammation, cancer, and malaria. In brief, this review article focuses on the broad pharmacological applications and the summary of the structure-activity relationship of molecules which can be employed to further explore the structure of diarylpentadienone. The current methodological developments towards the synthesis of diarylpentadienones are also discussed.

1,3-Thiazolidin-4-ones: Biological Potential, History, Synthetic Development and Green Methodologies

2018 ◽  
Vol 15 (8) ◽  
pp. 1109-1123
Author(s):  
Jonas da Silva Santos ◽  
Joel Jones Junior ◽  
Flavia M. da Silva
Keyword(s):  
Quality Of Life ◽  
Green Chemistry ◽  
Functional Group ◽  
Biological Properties ◽  
Structural Theory ◽  
Molecular Structures ◽  
Biological Potential ◽  
Synthetic Methodologies ◽  
Over Time

Background: We present here the synthesis of 1,3-thiazolidin-4-one (1) and its functionalised analogues, such as the classical isosteres, glitazone (1,3-thiazolidine-2,4-dione) (2), rhodanine (2-thioxo-1,3- thiazolidin-4-one) (3) and pseudothiohydantoin (2-imino-1,3-thiazolidin-4-one) (4) started in the midnineteenth century to the present day (1865-2018). Objective: The review focuses on the differences in the representation of the molecular structures discussed here over time since the first discussions about the structural theory by Kekulé, Couper and Butlerov. Moreover, advanced synthesis methodologies have been developed for obtaining these functional group, including green chemistry. We discuss about its structure and stability and we show the great biological potential. Conclusion: The 1,3-thiazolidin-4-one nucleus and functionalised analogues such as glitazones (1,3- thiazolidine-2,4-diones), rhodanines (2-thioxo-1,3-thiazolidin-4-ones) and pseudothiohydantoins (2-imino-1,3- thiazolidine-2-4-ones) have great pharmacological importance, and they are already found in commercial pharmaceuticals. Studies indicate a promising future in the area of medicinal chemistry with potential activities against different diseases. The synthesis of these nuclei started in the mid-nineteenth century (1865), with the first discussions about the structural theory by Kekulé, Couper and Butlerov. The present study has demonstrated the differences in the representations of the molecular structures discussed here over time. Since then, various synthetic methodologies have been developed for obtaining these nuclei, and several studies on their structural and biological properties have been performed. Different studies with regards to the green synthesis of these compounds were also presented here. This is the result of the process of environmental awareness. Additionally, the planet Earth is already showing clear signs of depletion, which is currently decreasing the quality of life.

A de novo Synthesis of Oxindoles from Cyclohexanone-Derived γ-Keto-ester Acceptors Using a Desaturative Amination–Cyclization Approach

Synthesis ◽  
2021 ◽  
Author(s):  
Henry P. Caldora ◽  
Sebastian Govaerts ◽  
Shashikant U. Dighe ◽  
Oliver J. Turner ◽  
Daniele Leonori
Keyword(s):  
Amino Acids ◽  
Primary Amine ◽  
De Novo ◽  
Building Blocks ◽  
De Novo Synthesis ◽  
Keto Ester ◽  
Mild Conditions ◽  
Blockbuster Drug

Here we report a desaturative approach for oxindole synthesis. This method uses simple γ-ester-containing cyclohexanones and primary amine building blocks as coupling partners. A dual photoredox–cobalt manifold is used to generate a secondary aniline that, upon heating, cyclizes with the pendent ester functionality. The process operates under mild conditions and was applied to the modification of several amino acids, the blockbuster drug mexiletine, as well as the formation of dihydroquinolinones.

Synthesis of Complex Boron–Nitrogen Heterocycles Comprising Borylated Triazenes and Tetrazenes Under Mild Conditions

2019 ◽  
Vol 142 (2) ◽  
pp. 1065-1076 ◽  
Author(s):  
Dominic Prieschl ◽  
Guillaume Bélanger-Chabot ◽  
Xueying Guo ◽  
Maximilian Dietz ◽  
Marcel Müller ◽  
...  
Keyword(s):  
Nitrogen Heterocycles ◽  
Mild Conditions ◽  
Boron Nitrogen

From Amines to Alkynes – Lighting the Way

2018 ◽  
Author(s):  
Dorota Gryko ◽  
Michał Ociepa ◽  
Joanna Turkowska
Keyword(s):  
Primary Amine ◽  
Pyridinium Salts ◽  
Mechanistic Studies ◽  
Molecular Scaffolds ◽  
Metal Free ◽  
Mild Conditions ◽  
The Way

We present a metal-free photoredox strategy for the formation of Csp3-Csp bonds from redox-activated primary amine derivatives. The developed reaction of 2,4,6-triphenylpyridiniu salts with alkynyl tosylates, leading to functionalized alkynes , is easily scalable, offers broad substrate scope, high chemoselectivity, and mild conditions. Its potentials also highlighted by diversification of complex molecular scaffolds. Moreover, mechanistic studies contribute to the elucidation of unexpected differences in reactivity of primary, secondary and alkyl pyridinium salts.

From Amines to Alkynes – Lighting the Way

2018 ◽  
Author(s):  
Dorota Gryko ◽  
Michał Ociepa ◽  
Joanna Turkowska
Keyword(s):  
Primary Amine ◽  
Pyridinium Salts ◽  
Mechanistic Studies ◽  
Molecular Scaffolds ◽  
Metal Free ◽  
Mild Conditions ◽  
The Way

We present a metal-free photoredox strategy for the formation of Csp3-Csp bonds from redox-activated primary amine derivatives. The developed reaction of 2,4,6-triphenylpyridiniu salts with alkynyl tosylates, leading to functionalized alkynes , is easily scalable, offers broad substrate scope, high chemoselectivity, and mild conditions. Its potentials also highlighted by diversification of complex molecular scaffolds. Moreover, mechanistic studies contribute to the elucidation of unexpected differences in reactivity of primary, secondary and alkyl pyridinium salts.

Divergent Synthesis of Five-Membered Nitrogen Heterocycles via Cascade Reactions of 4-Arylfuroxans

Synthesis ◽  
2020 ◽  
Vol 52 (18) ◽  
pp. 2667-2678
Author(s):  
Leonid L. Fershtat ◽  
Daniil A. Chaplygin ◽  
Ivan V. Ananyev ◽  
Nina N. Makhova
Keyword(s):  
Ring Opening ◽  
Heterocyclic Compounds ◽  
Nitrogen Heterocycles ◽  
Cascade Reactions ◽  
Materials Chemistry ◽  
One Pot ◽  
Mild Conditions ◽  
Novel Method ◽  
High Yields

A novel method for the synthesis of a diverse series of functionally substituted five-membered heterocyclic compounds via atom-economic, regio-, and diastereoselective one-pot reaction cascade was developed. This approach involves a ring opening in 4-arylfuroxans to α-oximinoarylacetonitrile oxides followed by [3+2] cycloaddition to various dipolarophiles to afford multisubstituted isoxazoles and isoxazolines. Subsequent azole–azole rearrangement of (oximino)isoxazolines/-isoxazoles, which can be conducted in a one-pot manner, results into functionally substituted furazans formation. The developed protocol is operationally simple, proceeds in mild conditions and with high yields of target heterocyclic systems. Overall, this study represents a new mode of isoxazole and 1,2,5-oxadiazole functionalization strategy, which is useful in medicinal and materials chemistry.

Trifluoromethyl nitrogen heterocycles: synthetic aspects and potential biological targets

2016 ◽  
Vol 52 (15) ◽  
pp. 3077-3094 ◽  
Author(s):  
F. Meyer
Keyword(s):  
Nitrogen Heterocycles ◽  
Biological Targets ◽  
Synthetic Methodologies

The synthetic methodologies and the potential biological targets of α-trifluoromethylated nitrogen heterocycles are presented.

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